2-[(4-Chloro-benz-yl)sulfan-yl]-4-(2-methyl-prop-yl)-6-(phenyl-sulfan-yl)pyrimidine-5-carbonitrile.

In the title compound, C(22)H(20)ClN(3)S(2), the S-bound benzene rings are inclined [dihedral angles = 78.13 (10) and 36.70 (9)°] with respect to the pyrimidine ring. The methyl-propyl group occupies a position normal to the pyrimidine ring [N-C-C-C torsion angle = 92.3 (2)°]. In the crystal, supra-molecular layers are formed in the bc plane, being consolidated by C-H⋯π and π-π inter-actions, the latter between the pyrimidine and S-bound benzene rings [inter-centroid distance = 3.7683 (12) Å].

Related literature

For the chemotherapeutic activity of pyrimidine derivatives, see: Al-Abdullah et al. (2011 ▶); Brunelle et al. (2007 ▶); Ding et al. (2006 ▶); Al-Safarjalani et al. (2005 ▶). For a related pyrimidine structure, see: El-Emam et al. (2011 ▶).

Experimental

Crystal data

C22H20ClN3S2

M = 425.98

Monoclinic,

a = 13.7771 (2) Å

b = 8.4961 (1) Å

c = 18.5878 (2) Å

β = 97.559 (1)°

V = 2156.82 (5) Å3

Z = 4

Cu Kα radiation

μ = 3.47 mm−1

T = 294 K

0.35 × 0.30 × 0.25 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.611, T max = 1.000

15819 measured reflections

4512 independent reflections

4113 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.117

S = 1.04

4512 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.46 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) general, I. DOI: 10.1107/S1600536812025810/pv2554sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025810/pv2554Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812025810/pv2554Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H20ClN3S2	F(000) = 888
Mr = 425.98	Dx = 1.312 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 8707 reflections
a = 13.7771 (2) Å	θ = 3.8–76.4°
b = 8.4961 (1) Å	µ = 3.47 mm−1
c = 18.5878 (2) Å	T = 294 K
β = 97.559 (1)°	Prism, colourless
V = 2156.82 (5) Å3	0.35 × 0.30 × 0.25 mm
Z = 4

Agilent SuperNova Dual diffractometer with Atlas detector	4512 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	4113 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.018
Detector resolution: 10.4041 pixels mm-1	θmax = 76.6°, θmin = 4.8°
ω scan	h = −16→17
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −10→10
Tmin = 0.611, Tmax = 1.000	l = −23→22
15819 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.117	w = 1/[σ2(Fo2) + (0.0576P)2 + 0.7026P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
4512 reflections	Δρmax = 0.41 e Å−3
254 parameters	Δρmin = −0.46 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0033 (3)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	0.54678 (4)	0.70944 (6)	0.73269 (3)	0.06701 (18)
S2	0.49600 (3)	0.22299 (6)	0.55116 (3)	0.06114 (16)
Cl1	0.03279 (4)	0.03665 (9)	0.36870 (4)	0.0973 (2)
N1	0.53172 (10)	0.46391 (16)	0.64164 (8)	0.0477 (3)
N2	0.66645 (10)	0.30012 (16)	0.61951 (8)	0.0505 (3)
N3	0.80681 (16)	0.6954 (3)	0.78507 (12)	0.0912 (7)
C1	0.57237 (12)	0.34328 (19)	0.61056 (9)	0.0466 (3)
C2	0.59250 (12)	0.55031 (19)	0.68709 (9)	0.0474 (4)
C3	0.69249 (12)	0.5177 (2)	0.70000 (9)	0.0483 (4)
C4	0.72740 (11)	0.3888 (2)	0.66431 (9)	0.0466 (4)
C5	0.83447 (12)	0.3509 (2)	0.67331 (10)	0.0541 (4)
H5A	0.8431	0.2392	0.6652	0.065*
H5B	0.8631	0.3749	0.7226	0.065*
C6	0.88789 (13)	0.4457 (2)	0.61966 (11)	0.0578 (4)
H6	0.8652	0.5549	0.6198	0.069*
C7	0.86479 (17)	0.3820 (3)	0.54342 (12)	0.0774 (6)
H7A	0.8969	0.4452	0.5109	0.116*
H7B	0.7953	0.3850	0.5289	0.116*
H7C	0.8874	0.2753	0.5421	0.116*
C8	0.99730 (16)	0.4440 (4)	0.64422 (16)	0.0962 (9)
H8A	1.0300	0.5050	0.6112	0.144*
H8B	1.0208	0.3375	0.6450	0.144*
H8C	1.0104	0.4882	0.6920	0.144*
C9	0.75677 (14)	0.6152 (3)	0.74776 (11)	0.0616 (5)
C10	0.42250 (13)	0.7160 (2)	0.69300 (10)	0.0532 (4)
C11	0.39312 (19)	0.8248 (3)	0.63982 (13)	0.0737 (6)
H11	0.4385	0.8918	0.6229	0.088*
C12	0.2950 (2)	0.8330 (3)	0.61170 (15)	0.0912 (8)
H12	0.2744	0.9069	0.5760	0.109*
C13	0.22799 (19)	0.7338 (3)	0.63589 (14)	0.0811 (7)
H13	0.1623	0.7404	0.6166	0.097*
C14	0.25756 (15)	0.6249 (3)	0.68832 (13)	0.0698 (5)
H14	0.2122	0.5564	0.7042	0.084*
C15	0.35460 (14)	0.6169 (2)	0.71770 (11)	0.0592 (4)
H15	0.3744	0.5445	0.7542	0.071*
C16	0.37985 (15)	0.3241 (3)	0.55162 (13)	0.0707 (6)
H16A	0.3653	0.3319	0.6011	0.085*
H16B	0.3852	0.4301	0.5331	0.085*
C17	0.29733 (13)	0.2398 (2)	0.50618 (10)	0.0530 (4)
C18	0.20723 (15)	0.2336 (3)	0.53091 (11)	0.0636 (5)
H18	0.2008	0.2733	0.5767	0.076*
C19	0.12653 (15)	0.1699 (3)	0.48935 (12)	0.0672 (5)
H19	0.0663	0.1673	0.5068	0.081*
C20	0.13592 (14)	0.1106 (2)	0.42242 (11)	0.0604 (5)
C21	0.22472 (16)	0.1110 (3)	0.39687 (11)	0.0685 (5)
H21	0.2309	0.0679	0.3517	0.082*
C22	0.30503 (15)	0.1760 (3)	0.43874 (11)	0.0636 (5)
H22	0.3653	0.1769	0.4213	0.076*

	U11	U22	U33	U12	U13	U23
S1	0.0521 (3)	0.0639 (3)	0.0867 (4)	−0.0022 (2)	0.0151 (2)	−0.0328 (2)
S2	0.0492 (3)	0.0598 (3)	0.0739 (3)	0.00163 (18)	0.0062 (2)	−0.0236 (2)
Cl1	0.0661 (3)	0.0886 (4)	0.1270 (6)	0.0010 (3)	−0.0249 (3)	−0.0215 (4)
N1	0.0413 (7)	0.0467 (7)	0.0565 (8)	−0.0006 (5)	0.0117 (6)	−0.0069 (6)
N2	0.0446 (7)	0.0483 (7)	0.0603 (8)	0.0020 (6)	0.0134 (6)	−0.0042 (6)
N3	0.0757 (13)	0.1114 (17)	0.0859 (13)	−0.0333 (12)	0.0085 (10)	−0.0302 (12)
C1	0.0442 (8)	0.0445 (8)	0.0527 (8)	−0.0004 (6)	0.0123 (6)	−0.0034 (7)
C2	0.0440 (8)	0.0463 (8)	0.0545 (9)	−0.0042 (6)	0.0163 (7)	−0.0049 (7)
C3	0.0430 (8)	0.0529 (9)	0.0506 (8)	−0.0079 (7)	0.0123 (6)	−0.0027 (7)
C4	0.0413 (8)	0.0495 (8)	0.0510 (8)	−0.0007 (6)	0.0133 (6)	0.0049 (7)
C5	0.0421 (8)	0.0611 (10)	0.0600 (10)	0.0032 (7)	0.0099 (7)	0.0072 (8)
C6	0.0439 (9)	0.0626 (10)	0.0695 (11)	0.0016 (8)	0.0172 (8)	0.0068 (9)
C7	0.0677 (13)	0.1020 (18)	0.0650 (12)	0.0075 (12)	0.0184 (10)	0.0083 (12)
C8	0.0482 (11)	0.144 (3)	0.0971 (18)	−0.0158 (14)	0.0143 (11)	0.0087 (18)
C9	0.0500 (9)	0.0742 (12)	0.0629 (11)	−0.0112 (9)	0.0153 (8)	−0.0114 (10)
C10	0.0537 (9)	0.0465 (9)	0.0624 (10)	0.0039 (7)	0.0183 (8)	−0.0125 (7)
C11	0.0877 (15)	0.0614 (12)	0.0753 (13)	−0.0019 (11)	0.0226 (12)	0.0039 (10)
C12	0.110 (2)	0.0811 (16)	0.0783 (15)	0.0204 (15)	−0.0029 (14)	0.0126 (13)
C13	0.0647 (13)	0.0928 (17)	0.0828 (15)	0.0155 (12)	−0.0022 (11)	−0.0145 (13)
C14	0.0537 (11)	0.0739 (13)	0.0844 (14)	−0.0014 (9)	0.0186 (10)	−0.0115 (11)
C15	0.0572 (10)	0.0526 (10)	0.0701 (11)	0.0050 (8)	0.0168 (9)	0.0003 (8)
C16	0.0530 (10)	0.0725 (13)	0.0839 (14)	0.0089 (9)	−0.0012 (9)	−0.0261 (11)
C17	0.0493 (9)	0.0534 (9)	0.0558 (9)	0.0030 (7)	0.0048 (7)	−0.0034 (8)
C18	0.0588 (11)	0.0810 (13)	0.0525 (10)	0.0087 (10)	0.0126 (8)	−0.0025 (9)
C19	0.0480 (10)	0.0773 (13)	0.0777 (13)	0.0024 (9)	0.0139 (9)	0.0035 (11)
C20	0.0525 (10)	0.0521 (10)	0.0736 (12)	0.0029 (8)	−0.0033 (8)	0.0005 (9)
C21	0.0693 (12)	0.0758 (13)	0.0603 (11)	−0.0030 (10)	0.0081 (9)	−0.0163 (10)
C22	0.0552 (10)	0.0750 (12)	0.0633 (11)	−0.0053 (9)	0.0177 (8)	−0.0113 (10)

S1—C2	1.7559 (16)	C8—H8C	0.9600
S1—C10	1.774 (2)	C10—C11	1.375 (3)
S2—C1	1.7508 (17)	C10—C15	1.382 (3)
S2—C16	1.817 (2)	C11—C12	1.386 (4)
Cl1—C20	1.743 (2)	C11—H11	0.9300
N1—C2	1.330 (2)	C12—C13	1.369 (4)
N1—C1	1.335 (2)	C12—H12	0.9300
N2—C4	1.335 (2)	C13—C14	1.366 (4)
N2—C1	1.336 (2)	C13—H13	0.9300
N3—C9	1.138 (3)	C14—C15	1.378 (3)
C2—C3	1.395 (2)	C14—H14	0.9300
C3—C4	1.398 (2)	C15—H15	0.9300
C3—C9	1.432 (2)	C16—C17	1.505 (3)
C4—C5	1.498 (2)	C16—H16A	0.9700
C5—C6	1.542 (2)	C16—H16B	0.9700
C5—H5A	0.9700	C17—C18	1.380 (3)
C5—H5B	0.9700	C17—C22	1.382 (3)
C6—C7	1.511 (3)	C18—C19	1.378 (3)
C6—C8	1.516 (3)	C18—H18	0.9300
C6—H6	0.9800	C19—C20	1.364 (3)
C7—H7A	0.9600	C19—H19	0.9300
C7—H7B	0.9600	C20—C21	1.369 (3)
C7—H7C	0.9600	C21—C22	1.381 (3)
C8—H8A	0.9600	C21—H21	0.9300
C8—H8B	0.9600	C22—H22	0.9300
C2—S1—C10	102.20 (8)	C11—C10—S1	119.80 (16)
C1—S2—C16	100.23 (9)	C15—C10—S1	120.09 (15)
C2—N1—C1	115.71 (14)	C10—C11—C12	119.1 (2)
C4—N2—C1	116.30 (14)	C10—C11—H11	120.5
N1—C1—N2	127.73 (15)	C12—C11—H11	120.5
N1—C1—S2	118.00 (12)	C13—C12—C11	120.8 (2)
N2—C1—S2	114.27 (12)	C13—C12—H12	119.6
N1—C2—C3	121.65 (15)	C11—C12—H12	119.6
N1—C2—S1	119.73 (12)	C14—C13—C12	120.0 (2)
C3—C2—S1	118.62 (13)	C14—C13—H13	120.0
C2—C3—C4	117.89 (15)	C12—C13—H13	120.0
C2—C3—C9	120.51 (16)	C13—C14—C15	120.0 (2)
C4—C3—C9	121.59 (16)	C13—C14—H14	120.0
N2—C4—C3	120.71 (15)	C15—C14—H14	120.0
N2—C4—C5	118.54 (15)	C14—C15—C10	120.1 (2)
C3—C4—C5	120.72 (16)	C14—C15—H15	119.9
C4—C5—C6	111.24 (15)	C10—C15—H15	119.9
C4—C5—H5A	109.4	C17—C16—S2	111.90 (14)
C6—C5—H5A	109.4	C17—C16—H16A	109.2
C4—C5—H5B	109.4	S2—C16—H16A	109.2
C6—C5—H5B	109.4	C17—C16—H16B	109.2
H5A—C5—H5B	108.0	S2—C16—H16B	109.2
C7—C6—C8	110.93 (18)	H16A—C16—H16B	107.9
C7—C6—C5	111.11 (17)	C18—C17—C22	117.82 (18)
C8—C6—C5	109.91 (18)	C18—C17—C16	118.50 (17)
C7—C6—H6	108.3	C22—C17—C16	123.56 (18)
C8—C6—H6	108.3	C19—C18—C17	121.52 (18)
C5—C6—H6	108.3	C19—C18—H18	119.2
C6—C7—H7A	109.5	C17—C18—H18	119.2
C6—C7—H7B	109.5	C20—C19—C18	119.33 (19)
H7A—C7—H7B	109.5	C20—C19—H19	120.3
C6—C7—H7C	109.5	C18—C19—H19	120.3
H7A—C7—H7C	109.5	C19—C20—C21	120.78 (19)
H7B—C7—H7C	109.5	C19—C20—Cl1	119.19 (16)
C6—C8—H8A	109.5	C21—C20—Cl1	120.02 (16)
C6—C8—H8B	109.5	C20—C21—C22	119.44 (19)
H8A—C8—H8B	109.5	C20—C21—H21	120.3
C6—C8—H8C	109.5	C22—C21—H21	120.3
H8A—C8—H8C	109.5	C21—C22—C17	121.07 (18)
H8B—C8—H8C	109.5	C21—C22—H22	119.5
N3—C9—C3	178.5 (3)	C17—C22—H22	119.5
C11—C10—C15	120.0 (2)
C2—N1—C1—N2	−0.4 (3)	C2—S1—C10—C11	−100.58 (16)
C2—N1—C1—S2	179.05 (12)	C2—S1—C10—C15	82.29 (16)
C4—N2—C1—N1	−0.7 (3)	C15—C10—C11—C12	0.0 (3)
C4—N2—C1—S2	179.89 (12)	S1—C10—C11—C12	−177.11 (19)
C16—S2—C1—N1	2.66 (17)	C10—C11—C12—C13	−0.5 (4)
C16—S2—C1—N2	−177.85 (15)	C11—C12—C13—C14	0.0 (4)
C1—N1—C2—C3	1.2 (2)	C12—C13—C14—C15	1.1 (4)
C1—N1—C2—S1	−178.59 (12)	C13—C14—C15—C10	−1.6 (3)
C10—S1—C2—N1	−5.74 (16)	C11—C10—C15—C14	1.0 (3)
C10—S1—C2—C3	174.49 (14)	S1—C10—C15—C14	178.16 (15)
N1—C2—C3—C4	−0.9 (2)	C1—S2—C16—C17	−177.46 (16)
S1—C2—C3—C4	178.83 (12)	S2—C16—C17—C18	141.33 (18)
N1—C2—C3—C9	178.32 (17)	S2—C16—C17—C22	−42.7 (3)
S1—C2—C3—C9	−1.9 (2)	C22—C17—C18—C19	−1.7 (3)
C1—N2—C4—C3	0.9 (2)	C16—C17—C18—C19	174.6 (2)
C1—N2—C4—C5	−176.83 (15)	C17—C18—C19—C20	0.4 (3)
C2—C3—C4—N2	−0.2 (2)	C18—C19—C20—C21	1.3 (3)
C9—C3—C4—N2	−179.41 (16)	C18—C19—C20—Cl1	−177.69 (17)
C2—C3—C4—C5	177.52 (15)	C19—C20—C21—C22	−1.7 (3)
C9—C3—C4—C5	−1.7 (3)	Cl1—C20—C21—C22	177.29 (18)
N2—C4—C5—C6	92.3 (2)	C20—C21—C22—C17	0.4 (3)
C3—C4—C5—C6	−85.4 (2)	C18—C17—C22—C21	1.2 (3)
C4—C5—C6—C7	−73.9 (2)	C16—C17—C22—C21	−174.8 (2)
C4—C5—C6—C8	162.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg1i	0.98	2.92	3.789 (2)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C17–C22 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cg1i	0.98	2.92	3.789 (2)	148

Symmetry code: (i) .